(1S,2S,4R)-1-(4,5-dimethylfuran-2-yl)-1-hydroxy-2,4-dimethyl-5-phenylmethoxypentan-3-one | 134860-57-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,2S,4R)-1-(4,5-dimethylfuran-2-yl)-1-hydroxy-2,4-dimethyl-5-phenylmethoxypentan-3-one
• CAS: 134860-57-4
• 化学式: C₂₀H₂₆O₄
• 分子量: 330.424
• InChiKey: SNUGLRLEPLCQQO-SXGZJXTBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.99
• 重原子数：
  24.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  59.67
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1S,2S,4R)-1-(4,5-dimethylfuran-2-yl)-1-hydroxy-2,4-dimethyl-5-phenylmethoxypentan-3-one 在 tetramethylammonium triacetoxyborohydride 作用下， 以 溶剂黄146 、 乙腈 为溶剂， 反应 12.0h， 以100%的产率得到(1S,2R,3R,4R)-5-Benzyloxy-1-(4,5-dimethyl-furan-2-yl)-2,4-dimethyl-pentane-1,3-diol
  参考文献：
  名称：

  Asymmetric aldol reactions using chiral boron reagents: Application to the synthesis of tirandamycin A

  摘要：

  The bicyclic acetal 1, a key intermediate in previous synthetic studies on tirandamycin A, has been prepared in enantiomerically pure form starting from the (R)-ethylketone 2 and the aldehyde 3. A reagent controlled aldol reaction using (-)-(Ipc)2BOTf selectively gave the 1,2-syn-2,4-syn adduct 4, which was subsequently converted into 1 via the 1,3-anti diol 5.

  DOI：

  10.1016/s0040-4039(00)74320-6
• 作为产物：
  描述：

  4,5-二甲基-2-糠醛 、 在 pH₇ buffer 、 双氧水 作用下， 生成 (1R,2R,4R)-1-(4,5-dimethylfuran-2-yl)-1-hydroxy-2,4-dimethyl-5-phenylmethoxypentan-3-one 、 (1S,2S,4R)-1-(4,5-dimethylfuran-2-yl)-1-hydroxy-2,4-dimethyl-5-phenylmethoxypentan-3-one
  参考文献：
  名称：

  Asymmetric aldol reactions using chiral boron reagents: Application to the synthesis of tirandamycin A

  摘要：

  The bicyclic acetal 1, a key intermediate in previous synthetic studies on tirandamycin A, has been prepared in enantiomerically pure form starting from the (R)-ethylketone 2 and the aldehyde 3. A reagent controlled aldol reaction using (-)-(Ipc)2BOTf selectively gave the 1,2-syn-2,4-syn adduct 4, which was subsequently converted into 1 via the 1,3-anti diol 5.

  DOI：

  10.1016/s0040-4039(00)74320-6